European Journal of Organic Chemistry

Cover image for Vol. 2017 Issue 7

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Anne Nijs

Impact Factor: 3.068

ISI Journal Citation Reports © Ranking: 2015: 17/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

VIEW

  1. 1 - 33
  1. Microreviews

    1. Photocatalysis

      Visible-Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp3)-Substrates

      Sara Roslin and Luke R. Odell

      Version of Record online: 20 FEB 2017 | DOI: 10.1002/ejoc.201601479

      Thumbnail image of graphical abstract

      The last few years have witnessed tremendous developments in the field of visible-light photocatalysis. This review summarizes recent advances in the functionalization of challenging unactivated radical precursors with an emphasis on the different classes of substrates now utilizable.

  2. Front Cover

    1. You have free access to this content
      Front Cover: Synthesis of Covalently Linked Oligo(phenyleneethynylene) Wires Incorporating Dithiafulvene Units: Redox-Active “H-Cruciforms” (Eur. J. Org. Chem. /2017)

      Frederik Præstholm Jørgensen, Johannes F. Petersen, Cecilie Lindholm Andersen, Anders B. Skov, Martyn Jevric, Ole Hammerich and Mogens Brøndsted Nielsen

      Version of Record online: 17 FEB 2017 | DOI: 10.1002/ejoc.201700230

      Thumbnail image of graphical abstract

      The cover picture shows H-cruciform-shaped molecules containing an OPV2-extended tetrathiafulvalene with orthogonally situated OPE3 or OPE5 units, which are of interest as electrically conducting molecular wires. On the left is a bronze figure of presumably the old Norse god Thor who is associated with thunder and lightning when striking his hammer, which in this figure has a cruciform-like shape. The figure is at the National Museum of Iceland, and we are grateful to the museum’s photograph collections manager Inga Lára Baldvinsdóttir for providing us with the photo. Details are discussed in the Full Paper by M. B. Nielsen et al. on page -- ff (DOI: 10.1002/ejoc.201601367).

  3. Full Papers

    1. Photo-Redox Catalysis

      Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide-Functionalised Carbon Nitride

      Andreas Uwe Meyer, Vincent Wing-hei Lau, Burkhard König and Bettina V. Lotsch

      Version of Record online: 16 FEB 2017 | DOI: 10.1002/ejoc.201601637

      Thumbnail image of graphical abstract

      The cyanamide-functionalised carbon nitride (NCN-CNx) can act as a photocatalyst for the sulfonylation of alkenes with sulfinate salts with product yields comparable to those obtained with the benchmark Eosin Y, while benefiting from the advantages of heterogeneous catalysis, i.e. ease of catalyst recovery for multiple re-use.

  4. Communications

    1. Photoredox Catalysis | Very Important Paper

      Photoredox-Catalyzed Cyclopropanation of Michael Acceptors

      Ana M. del Hoyo and Marcos García Suero

      Version of Record online: 16 FEB 2017 | DOI: 10.1002/ejoc.201601604

      Thumbnail image of graphical abstract

      A new protocol for the cyclopropanation of α,β-unsaturated carbonyl compounds with simple diiodomethane has been developed by means of photoredox catalysis. The process involves the photocatalytic generation of the iodomethyl radical, a novel carbenoid species able to transfer a CH2 group to a wide variety of Michael acceptors in a stereocontrolled manner.

  5. Microreviews

    1. Natural Product Synthesis

      Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products

      Gregg M. Schwarzwalder and Christopher D. Vanderwal

      Version of Record online: 16 FEB 2017 | DOI: 10.1002/ejoc.201601418

      Thumbnail image of graphical abstract

      The wealth of different strategies for the chemical synthesis of the halenaquinol/xestoquinol family of natural products is discussed. Similar themes throughout the different achievements are highlighted, and a discussion of the recently discovered relative exiguaquinol is included.

  6. Front Cover

    1. You have free access to this content
      Front Cover: Sphaericin, a Lasso Peptide from the Rare Actinomycete Planomonospora sphaerica (Eur. J. Org. Chem. /2017)

      Shinya Kodani, Yuto Inoue, Masahiro Suzuki, Hideo Dohra, Tomohiro Suzuki, Hikaru Hemmi and Mayumi Ohnishi-Kameyama

      Version of Record online: 15 FEB 2017 | DOI: 10.1002/ejoc.201700191

      Thumbnail image of graphical abstract

      The cover picture shows the three-dimensional solution structure of a new lasso peptide sphaericin. Lasso peptides are a class of natural occurring peptides, which possess an isopeptide bond and a common knot structural motif. The uniqueness of a lasso peptide is the three-dimensional structure with a tail part that forms a loop through its own ring. A new lasso peptide named sphaericin was isolated as an antibacterial principle from the rare actinomycete Planomonospora sphaerica. Calculations based on NOE experiments revealed that sphaericin possesses a typical lasso-peptide fold with a ring, a loop, and a tail. Details are discussed in the Full Paper by S. Kodani et al. on page -- ff (DOI: 10.1002/ejoc.201601334).

  7. Communications

    1. Organic Dyes

      Erythrosine B Catalyzed Visible-Light Photoredox Arylation–Cyclization of N-Alkyl-N-aryl-2-(trifluoromethyl)acrylamides to 3-(Trifluoromethyl)indolin-2-one Derivatives

      Zsombor Gonda, Ferenc Béke, Orsolya Tischler, Milán Petró, Zoltán Novák and Balázs L. Tóth

      Version of Record online: 10 FEB 2017 | DOI: 10.1002/ejoc.201601493

      Thumbnail image of graphical abstract

      Erythrosine B has been utilized as a novel photoredox sensitizer in the arylation-cyclization reaction of N-alkyl-N-aryl-2-(trifluoromethyl)acrylamides to indolin-2-ones. Arenediazonium tetrafluoroborates served as the source aryl radicals under the irradiation of blue LEDs at –50 °C. The scope and the limitations were investigated, and 27 examples (up to 83 % yield) are presented.

  8. Microreviews

    1. Photoredox Catalysis

      Proton-Coupled Electron Transfer in Photoredox Catalytic Reactions

      Norbert Hoffmann

      Version of Record online: 7 FEB 2017 | DOI: 10.1002/ejoc.201601445

      Thumbnail image of graphical abstract

      Proton-coupled electron transfer facilitates partial steps in photoredox catalytic reactions when corresponding electron transfer is endergonic. The scope of such reactions is considerably enlarged by such processes.

    2. Desymmetrization

      Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis

      Matthew A. Horwitz and Jeffrey S. Johnson

      Version of Record online: 7 FEB 2017 | DOI: 10.1002/ejoc.201601481

      Thumbnail image of graphical abstract

      Three distinct modes of diastereotopic group selection in natural product synthesis are reviewed. Case studies that enable the rapid buildup of stereochemical complexity by means of local desymmetrization are emphasized.

  9. Full Papers

    1. Photocatalytic Mechanism

      Metal-Free Photocatalytic Reductive Dehalogenation Using Visible-Light: A Time-Resolved Mechanistic Study

      Rebeca Martinez-Haya, Miguel A. Miranda and M. Luisa Marin

      Version of Record online: 7 FEB 2017 | DOI: 10.1002/ejoc.201601494

      Thumbnail image of graphical abstract

      The reductive dehalogenation of organic bromides has been achieved by using riboflavin (RF) as photocatalyst under visible-light irradiation. The viability of the different competing processes on the timescale of the corresponding RF excited states and RF radical anion were evaluated by time-resolved techniques. Thus, the key role of the RF radical anion has been proven.

    2. Photocatalysis

      Quantitative Profiling of the Heavy-Atom Effect in BODIPY Dyes: Correlating Initial Rates, Atomic Numbers, and 1O2 Quantum Yields

      Yannick P. Rey, Dario G. Abradelo, Nico Santschi, Cristian A. Strassert and Ryan Gilmour

      Version of Record online: 7 FEB 2017 | DOI: 10.1002/ejoc.201601372

      Thumbnail image of graphical abstract

      A GC-based method to assess catalyst performance is developed and validated with a set of halogenated BODIPY scaffolds. An initial-rate approximation is applied to a model transformation, and the trend follows the heavy-atom effect (v0,H < v0,Cl < v0,Br < v0,I). This approach is corroborated by determinations of absolute 1O2 and photoluminescent quantum yields and time-resolved luminescence decays.

  10. Communications

    1. Nitrogen Radicals

      Visible-Light-Mediated 5-exo-dig Cyclizations of Amidyl Radicals

      Daniel Fernandez Reina, Elizabeth M. Dauncey, Sara P. Morcillo, Thomas D. Svejstrup, Mihai V. Popescu, James J. Douglas, Nadeem S. Sheikh and Daniele Leonori

      Version of Record online: 6 FEB 2017 | DOI: 10.1002/ejoc.201601607

      Thumbnail image of graphical abstract

      Visible-light irradiation of electron-poor aryloxyamides in the presence of K2CO3 leads to the formation of amidyl radicals that undergo 5-exo-dig hydroamination–cyclization reactions to yield 5-methylene-pyrrolidinones.

    2. Strained Bioisosteres

      Schreiner's Thiourea Promoted [2+2] Cycloaddition of Captodative Azetidinones and Nitroolefins

      Zoltán Dobi, Tamás Holczbauer and Tibor Soós

      Version of Record online: 6 FEB 2017 | DOI: 10.1002/ejoc.201601524

      Thumbnail image of graphical abstract

      Strained, captodative benzylideneazetidinones function as potent reaction partners in thermal [2+2] cycloadditions with nitro alkenes. Strain relief during the cycloaddition can be leveraged to secure kinetic and thermodynamic stability for the aminonitrocyclobutane ring. Accordingly, this mild and robust procedure can be used to simplify the synthesis of azaspiro[3.3]heptane bioisoteres.

  11. Full Papers

    1. Synthetic Methods

      Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol

      Nieves P. Ramirez and Jose C. Gonzalez-Gomez

      Version of Record online: 31 JAN 2017 | DOI: 10.1002/ejoc.201601478

      Thumbnail image of graphical abstract

      The decarboxylative alkylation of carboxylic acids can be efficiently promoted by visible light under air at room temperature by using 9-mesitylene-10-methylacridinium perchlorate ([Acr-Mes]ClO4) as photocatalyst. A range of readily available starting materials are well tolerated in this transition-metal-free protocol.

    2. Lasso Peptides

      Sphaericin, a Lasso Peptide from the Rare Actinomycete Planomonospora sphaerica

      Shinya Kodani, Yuto Inoue, Masahiro Suzuki, Hideo Dohra, Tomohiro Suzuki, Hikaru Hemmi and Mayumi Ohnishi-Kameyama

      Version of Record online: 31 JAN 2017 | DOI: 10.1002/ejoc.201601334

      Thumbnail image of graphical abstract

      The lasso peptide sphaericin is isolated from the rare actinomycete Planomonospora sphaerica. The three-dimensional structure of sphaericin is determined to be the typical lasso structure by NOE experiments.

  12. Microreviews

    1. Sigmatropic Rearrangements

      The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C–N Bonds

      Pierre-Antoine Nocquet, Sylvain Henrion, Aurélie Macé, Bertrand Carboni, Jose Manuel Villalgordo and François Carreaux

      Version of Record online: 31 JAN 2017 | DOI: 10.1002/ejoc.201601316

      Thumbnail image of graphical abstract

      The allyl cyanate/isocyanate rearrangement represents a powerful strategy for the construction of the allyl isocyanate moiety. An overview of the main synthetic applications from the pioneering work of Ichikawa to the recent uses in natural products synthesis is presented in this microreview.

  13. Full Papers

    1. Silver Catalysis | Very Important Paper

      Sequential Silver-Catalyzed Oxidative Cyclization Reactions of Unprotected 2-Alkynylanilines to Anthranils

      Antonio Arcadi, Marco Chiarini, Luana Del Vecchio, Fabio Marinelli and Véronique Michelet

      Version of Record online: 30 JAN 2017 | DOI: 10.1002/ejoc.201601600

      Thumbnail image of graphical abstract

      The scope and limitations of the unusual silver-catalyzed oxidative cyclizations of 2-alkynylanilines to 2,1-benzisoxazoles are studied.

    2. Scholl Oxidative Coupling | Very Important Paper

      Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

      Mark S. Little, Stephen G. Yeates, Aula A. Alwattar, Kane W. J. Heard, James Raftery, Alyn C. Edwards, Adam. V. S. Parry and Peter Quayle

      Version of Record online: 30 JAN 2017 | DOI: 10.1002/ejoc.201601580

      Thumbnail image of graphical abstract

      Scholl coupling reactions proceed by unexpected oxidation/coupling pathways.

  14. Communications

    1. Photocatalysis

      Porphyrin-Catalyzed Photochemical C–H Arylation of Heteroarenes

      Katarzyna Rybicka-Jasińska, Burkhard König and Dorota Gryko

      Version of Record online: 27 JAN 2017 | DOI: 10.1002/ejoc.201601518

      Thumbnail image of graphical abstract

      Porphyrins are suitable photoredox catalysts for the direct C–H arylation of heteroarenes with aryl diazonium salts. The reaction involves photoelectron transfer from a porphyrin in its exited state to a diazonium salt.

  15. Full Papers

    1. Photoredox Catalysis

      A Photocatalytic Meerwein Approach to the Synthesis of Isochromanones and Isochromenones

      Stefano Crespi, Stefanie Jäger, Burkhard König and Maurizio Fagnoni

      Version of Record online: 27 JAN 2017 | DOI: 10.1002/ejoc.201601458

      Thumbnail image of graphical abstract

      A mild and facile photoredox approach towards synthetically interesting isochromanones and isochromenones is presented. The diazonium salts of various functionalised anthranilic acids have been converted by reaction with various alkenes into the desired bi- and tricyclic compounds in good to excellent yields.

  16. Communications

    1. Organocatalysis

      Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism

      Adriane A. Pereira, Amanda S. Pereira, Amanda C. de Mello, Arthur G. Carpanez, Bruno A. C. Horta and Giovanni W. Amarante

      Version of Record online: 27 JAN 2017 | DOI: 10.1002/ejoc.201601613

      Thumbnail image of graphical abstract

      The methylsulfenylation of activated carbons is now possible by using DMSO. A combined metal-free process and microwave irradiation allow chemoselective C–S bond formation.

  17. Full Papers

    1. Visible-Light Photocycloaddition

      Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes

      Michael Jirásek, Karolína Straková, Tomáš Neveselý, Eva Svobodová, Zdeňka Rottnerová and Radek Cibulka

      Version of Record online: 26 JAN 2017 | DOI: 10.1002/ejoc.201601377

      Thumbnail image of graphical abstract

      The photoorganocatalytic [2+2] cycloaddition of dienes mediated by flavin derivative 1 and visible light affords a variety of aza and thia analogues of bicyclo[3.2.0]heptanes with high diastereoselectivities.

    2. Porphyrinoid Chemistry

      Surprising Outcomes of Classic Ring-Expansion Conditions Applied to Octaethyloxochlorin, 2. Beckmann-Rearrangement Conditions

      Ruoshi Li, Eileen Meehan, Mathias Zeller and Christian Brückner

      Version of Record online: 24 JAN 2017 | DOI: 10.1002/ejoc.201601424

      Thumbnail image of graphical abstract

      Application of acidic or basic Beckmann-rearrangement conditions to the oxime of octaethyloxochlorin led to an abnormal Beckmann rearrangement and eventually formed a ring-expanded porpholactone or, using alternative reaction conditions, a 2-iminoporphyrin, respectively.

    3. Surprising Outcomes of Classic Ring-Expansion Conditions Applied to Octaethyloxochlorin, 3. Schmidt-Reaction Conditions

      Ruoshi Li, Mathias Zeller, Torsten Bruhn and Christian Brückner

      Version of Record online: 24 JAN 2017 | DOI: 10.1002/ejoc.201601423

      Thumbnail image of graphical abstract

      Application of Schmidt-reaction conditions to octaethyloxochlorin led, depending on the mineral acid used, to either a loss of an ethyl group and the formation of an α-OH–ketochlorin, or to the step-wise and controlled chlorination of the meso-positions.

    4. Porphyrinoid Chemistry | Very Important Paper

      Surprising Outcomes of Classic Ring-Expansion Conditions Applied to Octaethyloxochlorin, 1. Baeyer–Villiger-Oxidation Conditions

      Ruoshi Li, Matthias Zeller and Christian Brückner

      Version of Record online: 24 JAN 2017 | DOI: 10.1002/ejoc.201601422

      Thumbnail image of graphical abstract

      Application of Baeyer–Villiger oxidations to oxochlorins did not lead to ring-expanded porphyrinods instead to meso- or N-oxidized products.

    5. Organocatalysis

      Green Organocatalytic Dihydroxylation of Alkenes

      Alexis Theodorou, Ierasia Triandafillidi and Christoforos G. Kokotos

      Version of Record online: 3 JAN 2017 | DOI: 10.1002/ejoc.201601144

      Thumbnail image of graphical abstract

      One-pot magic: A green organocatalytic one-pot procedure for the dihydroxylation of alkenes is described. The reaction proceeds through an intermolecular ring opening of the in situ prepared epoxide in the presence of water to lead to the desired product. A variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in excellent yields.

  18. Communications

    1. Photoredox Catalysis

      Visible-Light, Photoredox-Mediated Oxidative Tandem Nitroso-Diels–Alder Reaction of Arylhydroxylamines with Conjugated Dienes

      Veronica Santacroce, Raphael Duboc, Max Malacria, Giovanni Maestri and Geraldine Masson

      Version of Record online: 30 DEC 2016 | DOI: 10.1002/ejoc.201601492

      Thumbnail image of graphical abstract

      A visible-light, photoredox-mediated oxidative tandem nitroso-Diels–Alder reaction generates 3,6-dihydro-1,2-oxazines from arylhydroxylamines and dienes via intermediary nitrosoarenes in the presence of Ru(bpy)3Cl2 (bpy = 2,2′-bipyridine).

  19. Microreviews

    1. Unactivated Olefins

      Emergence of Unactivated Olefins for the Synthesis of Olefinated Arenes

      Arghya Deb and Debabrata Maiti

      Version of Record online: 30 DEC 2016 | DOI: 10.1002/ejoc.201601253

      Thumbnail image of graphical abstract

      Overdependence on electronically biased activated olefins is a key drawback of Mizoroki–Heck and Fujiwara–Moritani coupling. With unbiased aliphatic olefins, inability to control regio- and stereoselectivity greatly restricts their application. Recent significant advances in olefination with unactivated alkenes to synthesize both linear and branched olefin products are outlined in this review.

  20. Communications

    1. Photochemical Flow Reactions

      Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors – Application to Photoredox and H-Atom-Transfer Chemistry

      Alexander M. Nauth, Alexander Lipp, Benjamin Lipp and Till Opatz

      Version of Record online: 28 DEC 2016 | DOI: 10.1002/ejoc.201601394

      Thumbnail image of graphical abstract

      “Sunflow” – The combination of a microcapillary reactor and sunlight enables fast and green photoredox and H-atom-transfer reactions in continuous flow. Kinetic studies reveal high reaction rates with a simple and inexpensive reactor setup (less than 90 USD acquisition value).

    2. Palladium-Catalyzed Amination

      Pd-PEPPSI-IPentCl-Catalyzed Amination Using Aminotriphenylsilane as an Ammonia Surrogate

      Christopher Lombardi, David Mitchell, Michael J. Rodriguez and Michael G. Organ

      Version of Record online: 28 DEC 2016 | DOI: 10.1002/ejoc.201601565

      Thumbnail image of graphical abstract

      Triphenylsilyl-protected anilines were obtained from the cross-coupling of aminotriphenylsilane with aryl halides in the presence of Pd-PEPPSI-IPentCl {dichloro(3-chloropyridyl)[4,5-dichloro-1,3-bis(2,6-dipent-3-ylphenyl)imidazol-2-ylidene]palladium(II)}. The silylated products were then alkylated without over-alkylation, yielding the secondary amines after hydrolysis under mild acidic conditions.

  21. Microreviews

    1. Metal-Catalysed Azidation

      You have full text access to this OnlineOpen article
      Metal-Catalysed Azidation of Organic Molecules

      Monalisa Goswami and Bas de Bruin

      Version of Record online: 22 DEC 2016 | DOI: 10.1002/ejoc.201601390

      Thumbnail image of graphical abstract

      The azide moiety is a desirable functionality in organic molecules, useful in a variety of transformations such as triazole synthesis, aziridination, C–H bond amination, isocyanate synthesis, the Staudinger reaction etc. This review highlights metal-catalysed azidation, which provides shorter routes to a variety of organic molecules of interest, with a focus on substrate scopes and mechanisms.

  22. Full Papers

    1. Molecular Wires

      Synthesis of Covalently Linked Oligo(phenyleneethynylene) Wires Incorporating Dithiafulvene Units: Redox-Active “H-Cruciforms”

      Frederik Præstholm Jørgensen, Johannes F. Petersen, Cecilie Lindholm Andersen, Anders B. Skov, Martyn Jevric, Ole Hammerich and Mogens Brøndsted Nielsen

      Version of Record online: 13 DEC 2016 | DOI: 10.1002/ejoc.201601367

      Thumbnail image of graphical abstract

      The synthesis of large π-conjugated motifs based on two parallel oligo(phenyleneethynylene)s (OPEs) and an orthogonally situated redox-active stilbene-extended tetrathiafulvalene (TTF) is presented. The OPEs are end-capped with thioester groups as potential electrode anchoring groups.

    2. Molecular Motors

      A Light- and Electricity-Driven Molecular Pushing Motor

      Christoph Burkhart and Gebhard Haberhauer

      Version of Record online: 13 DEC 2016 | DOI: 10.1002/ejoc.201601371

      Thumbnail image of graphical abstract

      Molecular pushing motors: A novel molecular motor running on clean stimuli (voltage and light) has been designed containing two independently switchable moieties, an azobenzene and a thianthrene. The former is triggered by light and the latter by voltage. The four states of the molecular motor were identified by quantum chemical methods and UV/Vis spectroscopy.

VIEW

  1. 1 - 33

SEARCH

SEARCH BY CITATION